Choose the windows
Pick two or three realistic windows around the commitments you already have. Decide the start point, transport and a shorter route in advance. Put that shorter option in the calendar next to the full outing.
Give each outing one job
An outing might be for getting outside, learning a route or meeting a friend. Give it one purpose. If the plan depends on exact splits and an empty route, keep an easier alternative for days when the path is busy.
Write down what matters
Log the date, time outside, route and a few words about how it felt. Note wind, ice or traffic if they affected your run. At the end of the week, use the notes to move an awkward time slot or swap a route you rarely use.